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The Slow Life as an Introvert

Millennials Share Their Tips for Working While Traveling the Globe from the Tailwind Blog

Is it possible to juggle a new career and travel at the same time? It’s often mistaken as a difficult task, maybe even impossible. But reality might surprise you. I’ve discovered the answer to this question for myself over the past year and a half as a fresh-faced graduate. I endeavored to continue working as a writer while maintaining a transient lifestyle. Having a new career and traveling is absolutely possible. Other millennials are making it happen, and so can you.

The following post was originally published on Tailwind Blog on April 11, 2016

When you’re still new to a career and trying to make a name for yourself on the job, it can be stressful to take vacation time.

Heck, forget traveling for pleasure—even business travel can feel stressful. When you’re juggling delayed flights or bad cell service with the desire to make a good impression on your clients and coworkers, travel can feel anything but relaxing.

But take a deep breath, because we’ve got some good news for you: You can travel the globe and continue to rock out at your job. Here’s how four hard-working millennials make it happen.

Jenn Hirsch. Photo credit Brandon Smith

Draw work inspiration from your travels.

As a surf retreat leader and a storyteller through (and founder of) Swell Story, Jenn Hirsch has learned firsthand that her travels can inform her work in big ways.

“My rule has always been to find inspiration from where you travel for whatever venture you have at present,” she says. “[My] work is highly creative yet grounded in the present—kind of like traveling to foreign countries and surfing in general.”

Communicate with your team before you leave.

Make sure your colleagues and clients have a sense of where you’ll be and what your availability will be like before you leave the office.

“Before a trip, I think it is important to meet with your team and third-party partners to make sure all bases are covered,” says Nolan Walsh, CEO of Thursday Boot Company.

Let folks know when you’ll be out of touch, and also aim to make yourself available at times when they’ll be working.

“I usually create a block of 3-5 hours that overlap with my work day back home,” says Hirsch. “This is a great tool to find overlapping time when you travel. Share your travel itinerary with your close team members, and let them know when you likely won’t be able to take calls. With advance communication, anything is possible.”

Use long transit times for work.

Instead of bemoaning the time you spend in transit, put it to productive use.

“You’re already stuck in a chair, and you’ll feel better getting work done than watching the in-flight movie you never really wanted to see,” says Walsh.

Bonus: Get work done on the plane or train, and you’ll have more free time to explore your destination.

Nolan Walsh at home in NYC

Stay charged.

The best hot spots and data plans won’t help you get work done if you can’t turn your devices on in the first place. Never underestimate the value of keeping your work gadgets fully juiced.

Embrace free time whenever it arises.

While business travel can take you to all corners of the globe, it can be tough to actually see those places when you’re sitting in meetings all day.

The solution? Go exploring whenever down time presents itself, says Hirsch, whether that’s during a midday lunch break or at the wee hours of the morning. Especially in major metropolitan areas (think London, Tokyo, or New York), there’s something to see no matter when you get a free moment. Don’t miss it.

Ricky Joshi (foreground) whitewater rafting in Tennessee

Mix business with pleasure.

“I really enjoy visiting places for business where I can add on a couple of extra days to explore an area,” says Ricky Joshi, co-founder and CMO of Saatva Mattress. “Los Angeles, Miami, and Chicago are great for this… I [also] really enjoy Central and South America, where I can go on a more adventurous trip. The Caribbean Island of St. Kitts and the Portland area of Jamaica are also personal favorites.”

It’s also smart to plan trips around your personal preferences.

“I’ve never fully adjusted to New York winters, so in Q1 and Q4 I’ll jump at any excuse to take a meeting or contract in Southern California,” says Ellis.

You’ll improve your mental state and your productivity if you go somewhere that inspires and uplifts you.

Roll with the punches.

Try discovering that your airline lost your luggage after you’ve touched down in Bolivia, as Joshi did. “Because I was so “off the grid,” it was so difficult finding a place to even try to call them to track it,” he says. “I finally gave into my fate and bought essentially a new, very light, wardrobe.”

It may not have been ideal, but Joshi made it work. When fate hands you lemons, go find yourself an orange.

Bonus: Practicing adaptability and efficient problem solving will serve you well on the job.

Charlie Ellis in Montana

Unplug every once in awhile.

It’s not a good idea to go MIA without letting clients and coworkers know you’ll be off the grid. But everyone—everyone—needs to unplug once in awhile, and that includes you. Do it responsibly by setting clear expectations before your digital detox, setting up an out-of-office email reply, and then committing yourself to not checking your email or phone, says Hirsch. Your mind will thank you for it.

Far from being a hassle, traveling as a millennial—for work or pleasure—doesn’t have to be a career killer. Communicate with your team, be open to expanding your horizons, and don’t forget to enjoy yourself. After all, there’s more to life than work.

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Erika is a writer and content creator exploring the globe boldly and slowly one destination at a time. Her travels and rich upbringing as an Asian-American fuel many of her stories where she endeavors to write about the human condition. Although she might presently call NE Florida home, her heart remains listless for her home in Maui. She is an advocate for "experiences over possessions," a Marquez fan, and a self-proclaimed introvert.